Tetrahydrofuran → HCID 56847974, compound

HRID 1798422Notes

Reaction equation

HRID 1798422 reaction equation
S=C1[N:6]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18](=[O:20])[CH3:19])=[C:13]([O:21][CH3:22])[CH:12]=2)=[O:8])[CH2:5][CH2:4]S1.[CH3:23][C:24](C)([CH3:28])[CH2:25]CN.C1COCC1>C(Cl)Cl>[C:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][O:9][C:7](=[O:8])[NH:6][CH2:5][CH2:4][C:24]([CH3:28])([CH3:25])[CH3:23])=[CH:12][C:13]=1[O:21][CH3:22])(=[O:20])[CH3:19]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 197093,3-DimethylbutylamineHCID 568478684-(Acetyloxy)-3-methoxybenzyl 2-thioxo-1,3-thiazolidine-3-carboxylate

Product 1

HCID 56847974HCID 56847974, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This compound was prepared from VII (288.5 mg, 0.845 mmol), 3,3-dimethylbutylamine (85.5 mg, 114 μL, 0.845 mmol) and anhydrous THF (4.2 mL) as described for 13. The reaction was complete within 2 hours. The reaction solution was diluted with CH2Cl2 and extracted with in 1N HCl and saturated NaCl. The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The crude material was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (7:3, v/v) to render 95.8 mg (35%) of 16 as an oil; 1HNMR (CDCl3) δ 6.99 (d, 3J=7.95 Hz, 1H), 6.95 (s, 1H), 6.92 (d, 3J=7.95 Hz, 1H), 5.04 (s, 2H), 4.60 (bs, 1H), 3.82 (s, 3H), 3.21-3.17 (m, 2H), 2.29 (s, 3H), 1.42-1.38 (m, 2H) and 0.91-0.90 (m, 9H). Exact mass (ESI) calculated for C17H26NO5 [M+H]=324.1805. found 324.1814.

Workup

  1. extractionextracted with in 1N HCl and saturated NaCl
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by column chromatography on silica gel eluting with hexanes/ethyl acetate (7:3

Sources & evidence

ORD record
ord-05d91961b27b4ca789bc2c3022401136
Source dataset
uspto-grants-2013_01
Patent number
US08343971B2

Reaction notes

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